Succinic-acid ether of cinchona alkaloids.



UNiTEn STATES PATENT Urrrcn.

HEINRICH THRON, OF FRANKFORT-ON-THE-MAIN, GERMANY, ASSIGNOR TO VERETNIGTE CHININFABRIKEN ZIMMER dt (30., GESELLSCHAFT MIT BE- SCHRANKTER HAFTUNG, OF FRANKFORT-ON-THE-MAIN, GERMANY.

SUGClNlC ACID ETHER OF CINCHONA ALKALOIDS.

SPECIFICATION forming part of Letters Patent No. 69 6,609, dated April 1, 1902.

Original application filed April 24:, 1901, Serial No. 57,322. Divided and this application filed January 8,1902. Serial No. 88,932. (No specimens.)

To 60% whom, it may concern:

Be it known that I, HEINRICH THRON, a subject of the Emperor of Germany, and a resident of Frankfort-on-the-Main, Germany,

have invented certain new and useful Improvements in Pharmaceutical Products, of which the following is a specification.

My invention relates to the production of hitherto unknown succinic-acid ethers of the cinchona alkaloids having in case quinin is used most probably the following formula:

and the present application is a divisional application from my original application, Serial No. 57,322, filed April 24, 1901, designed to cover specifically the preparation of the suc-. 2o cinic-acid ether of the cinchona alkaloids.

According to my researches these new compounds can be easily obtained by heating the alphylethers of succinic acid with the cinchona alkaloids. On using, for instance, the 2 5 phenolethers of succinic acid and quinin succinylquinin is obtained, which is tasteless and possesses great therapeutic value. The average dose employed for medicinal purposes is about two grams.

In carrying out my new process practically I can proceed as follows: 64.8 kilograms of anhydrous quinin are heated for several hours with twenty-seven kilograms or more of phenolether of succinic acid to a temperature of 130 to 140 centigrade. The new succinylquinin is then formed according to the following equation:

benzene.

with dilute alkali, Which removes'the phenol, and the new succinylquinin is then extracted from the benzene solution by diluted acid. By adding dilute ammonia to the acid solution and shaking with ether the succinylquinin is dissolved in the latter. After evaporation of the ether the succinylquinin can be crystallized out of dilute alcohol.

The new succinylquinin forms large nee.- dies, melting at 97 centigrade. It is nearly tasteless, very difflcultly soluble in water, readily soluble in alcohol, ether, benzene, and chloroform.

The new succinylquinin still retains basic properties and forms salts with organic and inorganic acids. These salts are also of great value in medicine, as the therapeutic eifect of the succinylquinin may be modified and reinforced by the proper selection of the acid with which the ether is combined. Thus the salicylate of succinylquinin will be very efficient in rheumatic affections, whereas the cinnamic-acid salt of the succinylquinin will be of great value in tuberculous affections.

Instead of the phenolether of succinic acid other alphylethers of succinic acid may be employed in the above process, and instead of the quinin other cinchona alkaloids, such as quinidin, may be used.

Having now described my invention and in what manner the same is to be performed, what I claim as new, and desire to secure by Letters Patent, is-

1. The herein-described new succinic-aeid others of the cinchona alkaloids being very difficultly soluble in water, readily soluble in alcohol, benzene, ether and chloroform, still possessing basic properties forming with organic and inorganic acids well-characterized salts, substantially as hereinbefore described.

2. The herein-described new succinic-acid ether of quinin having most probably the formula /OOO.C20H23N2O 0,11,,

oooo n mo forming nearly-tasteless needles, melting at name in the presence of two subscribing wit- .97 eentigrade very difficultly soluble in wanesses.

ter, readily soluble in alcohol, benzene, ether and chloroform; forming well-characterized HEINRICH THRON 5 salts with organic and inorganic acids, sub- Witnesses:

stantially as described herein. WILHELM EITEL,

In testimony whereof I have signed my THEOPHIL REGELMANN. 

